Episode #029

How to Win by Refusing to Quit with Tracy Osborn of Hello Web Design

Tracy Osborn once asked herself, "Should I learn how to code, or quit my startup?" You can guess which answer she chose, time and time again. Learn how relentless perseverance over time can help build a successful business.


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Courtland Allen 0h 0m 7s

What's up everybody? This is Courtland from IndieHackers.com where I talk to the founders of profitable internet businesses and I ask them about their challenges and hardships so the rest of us can learn from their mistakes instead of having to make them on our own.

Today I'm talking to Tracy Osborn. She's the founder of a company called Wedding Lovely and also a series of books known as the Hello Web books. A few of them deal with teaching non-programmers how to code, and the latest one helps programmers learn to become good designers.

My original goal with this interview was to spend the bulk of it talking to Tracy about design and some tips that non-designers could use to really make better looking websites, which is increasingly important in the world of today where it seems like every website is professionally designed. What actually ended up happening was that we started talking about Tracy's story as an entrepreneur and never really left that topic. I consider that a good thing because her story is so fascinating and educational. It's really a story that proves how far you can get by simply refusing to quit no matter what happens.

I actually saw a tweet today that said something to the tune of, if you want to be successful, pick any idea and work on it for 10 years. Tracy's story really is a great illustration of what that looks like. Apologies to you Tracy for not initially sticking to the topic that I planned on sticking to, but if you're a listener you really get two for the price of one because you listen to this excellent podcast and hear Tracy's story and you can head over to hellowebbooks.com and buy her book on web design afterwards. With that, let's start the episode.

Courtland Allen 0h 1m 32s

I'm here with Tracy Osborn. Tracy, thanks so much for coming on the show. It's a pleasure to have you.

Tracy Osborn 0h 1m 37s

Yeah. Thanks for having me.

Courtland Allen 0h 1m 39s

I don't know if you remember, but we ran into each other briefly way back in I think 2010 at the Y Combinator headquarters down in Mountain View. Do you remember that?

Tracy Osborn 0h 1m 48s

I was trying to think about which, I knew it was YC and I couldn't think, was it start up school or was it… If it was 2010, that must've been when my husband was going through YC because I just went to-

Courtland Allen 0h 1m 59s

Yeah. I think that might've been it.

Tracy Osborn 0h 2m 1s

Yeah. I just basically followed him along. This actually what got me into start ups is he had a start up, went through YC, and I was like whatever event you're going to I'm going to go to. I'm pretty sure Jessica Livingston thought I was part of YC during that time. I did a bunch of freelance work with other YC companies in that batch so I was at a bunch of the meetings and I went to all the events. This was also when YC was a lot smarter, so I use it to my advantage to make it look like I was a part of YC, which actually totally worked out. That was a really awesome summer and it was cool because I got to meet you. I guess that must've been…

Courtland Allen 0h 2m 35s

I think it was probably start up school because I ended up doing YC in winter 2011 in January and I went to start up school the fall beforehand. I think they had a whole bunch of events afterwards.

Tracy Osborn 0h 2m 44s

Yeah. The start up school had the invitation only events, maybe that was it.

Courtland Allen 0h 2m 51s

Yeah. Something like that. 2010 was a long time ago.

Tracy Osborn 0h 2m 54s

Seven years ago. It's crazy.

Courtland Allen 0h 2m 57s

I know. It's nuts. Don't remind me.

Tracy Osborn 0h 2m 59s

I know, right?

Courtland Allen 0h 3m 1s

Anyway, In the past six or seven years, it's hard for me to even know where to start this interview because you've done so much. You've taught yourself how to code, you've gone from that to giving keynotes at programming conferences like DjangoCon.

Tracy Osborn 0h 3m 15s

Just booked another one today actually.

Courtland Allen 0h 3m 16s

Yeah, that's nuts. You're an author. You self-published several books to help other people learn the basics of web programming so that they can build their own web apps and side projects. You started a company called Wedding Lovely, which perhaps is the best place to start because from what I can gather it seems like that was a genesis of a lot of the other things that you've done.

Tracy Osborn 0h 3m 34s

Yeah. There's a lot of people out there I talk to, and this is totally fine, someone's like, "Oh I worked at this job for two years, oh then I did this job for one year" so their life is kind of in these pieces. Mine just feels like this long string. It started with Wedding Lovely, I guess really before. It started with that summer when I followed Andre around Y Combinator and I got it in my head that I wanted to do a start up too, but I didn't know how to code.

There's a longer story here. I originally went to university for computer science and then rage quit because I hated programming in university. I just did not… We were learning Java and it was very university computer science where it's like let's take this sorting function and reverse engineer it and write a giant paper on it. I'm like this is the worst. I hate this.

I got an art degree and I vowed to never program again. I was just going to do, originally label a design and then I fell back into doing web design. The summer, watched Andre go through YC and I was like, "Oh that looks awesome. I want a start up too." as you do when you see that process. You only see the good things.

Courtland Allen 0h 3m 34s

Yeah. Of course.

Tracy Osborn 0h 4m 38s

Yeah. It started out with me trying to find my technical co-founder as you do as someone who doesn't know how to code. It was like three months, I did this Hacker News post that actually got to the top of Hacker News. Totally different world of Hacker News back then, like the fact that this thing got to the top of Hacker News. I was like, "I'm Tracy and I want to launch this start up and I'm looking for a technical co-founder." Everyone's like, "Wow how novel." I had like 80 emails and-

Courtland Allen 0h 4m 38s


Tracy Osborn 0h 5m 5s

I did this whole… Yeah. It was just like, I don't know, it was such a different time, this seven years ago.

Courtland Allen 0h 5m 11s

I can relate because I also found my co-founder in 2010 on Hacker News via a front page post.

Tracy Osborn 0h 5m 17s

It feels like Hacker News has evolved from that. It's so different.

Courtland Allen 0h 5m 22s

It's a lot bigger.

Tracy Osborn 0h 5m 23s

Yeah. Definitely. To cut this part of the story a little bit short, essentially I found someone, we got a YC interview, and then it fell apart that night. The night before the interview it just completely fell apart. Day of the interview we realized we didn't want to work together, did the interview anyways, didn't get into YC, and it was like, oh thank goodness because I wouldn't want to break up my co-founder the day of YC interview.

Then I was like, okay, if I actually want to launch this start up do I just learn how to code or quit? Essentially I was like I'm not going to do the whole co-founder process again. That's really what led me to picking up Python, much easier programming language to pick up than Java.

Courtland Allen 0h 6m 5s

Did you ever at any point in this process consider that you wouldn't learn to code but maybe you would just outsource and hire other people to write your code for you?

Tracy Osborn 0h 6m 13s

I think I wasn't really thinking about it as a start up. Then it was kind of like, I'm just going to launch this little website and try to figure it out. I'm pretty sure I was unemployed at this point and had time on my hands and not a lot of money. I think that's how it came about. I was like okay. Then Andre, the person I went with YC, he's a master Python programmer, and he was like, "Let me show you Python." Yeah. I don't think it ever came in my head to outsource this.

This is kind of my whole life is with the books and everything, I always just like, "Eh I'll just do it myself." I think I was just like, "Eh fine, I'll just program this myself." Picked up just enough Python and Django in order to build this… I don't know. It was a really basic website. It wasn't what I applied to YC for. The one I applied for YC is I wanted to build this service to help people build and design their wedding invitations online and then be able to print it at home, so someone who doesn't have design experience didn't have to outsource that part. I could just help them with that hard part, the design, and then let them print their own invitations.

To a new programmer, building something that could do something like build a typographically perfect wedding invitation, that was like, okay, I'm not going to learn enough programming to ever launch this probably. I basically just built this directory. I decided to just make it easier for people to connect with designers rather than replacing the designer. It was side project, I didn't really mean to turn it into a start up. This was probably late 2010, maybe early 2011. It's seven years later, it's hard to figure out when things started.

Courtland Allen 0h 7m 49s

How did you learn to code so fast? Was your husband, or your boyfriend at the time, helping you learn?

Tracy Osborn 0h 7m 54s

He did help me learn, basically in terms of Python, but I decided to use the framework Django because Django abstracts out a lot of things, like the whole database part. It basically makes it a lot simpler for someone who doesn't know what's going on in the back end in order to build a web app. This is actually how I started my books is I took this process of learning how to build a web app with Django and I was like okay that was really awesome, I want to help other people do the same thing.

When it comes to learning how to code, to this day I don't… That sounds like 100% thing, like I know how to code now. I basically learned about the 5% that I needed in order to launch just something really, really simple. I didn't know how to do anything else and so when I had to launch a new feature, I had to be like, okay crap, now I need to go learn how to do that in order to launch this feature for this website I had. It was kind of like learn by doing.

Courtland Allen 0h 8m 43s

That's the perfect way to learn I think.

Tracy Osborn 0h 8m 45s

Oh my God, yes.

Courtland Allen 0h 8m 46s

It's impossible to just sit down, read 10 books, memorize everything, and then come out of the other side a programmer, or anything else really.

Tracy Osborn 0h 8m 53s

Definitely. This is again jumping ahead to when I decided to write Hello Web App, it was because that whole learn by doing thing, it was like, oh crap that's like the best way of learning. Spoiler alert to the book series, this is like four years later of working at the start up, we can go back to Wedding Lovely, but essentially the book series, Hello Web App, it isn't like you're going to learn now to build a blog or you're going to learn how to build a polling app, something specific. I try to write it so people can use the examples in this book to write something that's unique to them and essentially they can make a directory clone or a Twitter clone or a Facebook clone or something like that. I call it a collection of objects because building something real, when you're trying to teach yourself how to code, building something that you actually care about, that's unique to you, I think is key for getting that information to stick in your head.

Courtland Allen 0h 9m 42s

The thing that you were building was your own website. Over the course of a fall and a winter you're learning to build everything that you need to get your new website out the door. What's the first thing that you did when you got to the point of thinking that hey this is good enough to actually get people using it?

Tracy Osborn 0h 9m 58s

Wedding Lovely is the company. Wedding Lovely today has 11 different websites. The website I had launched back then is called weddinginvitelove.com so it's part of the Wedding Lovely company as a whole. This is the first thing I launched so that was originally on its own.

Wedding Invite Love is a directory of wedding invitation designers. I decided not to constrain it to a specific location, which nowadays I wish I did because that would've made some things simpler. When I wrote it I was like, whatever, I don't know if people are going to use it so I'm going to let anyone sign up for it. It doesn't have to be in the US, it could be people in Canada. I had someone really early on from Israel and I let them know, I was like, "Ah, I don't think I'm going to be sending you any traffic." They're like, "Whatever it's free." I'm like, "Okay."

I wrote it so anyone could sign up and I launched it. I think I got 10 people to sign up for it. I was like, whatever, I'll just put it online now. It's essentially useless. If you went onto this website to try to find a wedding invitation designer and there's only 10 options and they're all over the US, it was useless. It was free and I asked people to sign up for it. I said, "Hey there's not going to be a lot of traffic for a while, but you'll get an SEO link." which to small businesses they're like, "Ooh that sounds fancy."

Courtland Allen 0h 11m 14s

Sure. Might as well.

Tracy Osborn 0h 11m 15s

Yeah. It's free, again. I just like, "Hey as we get rolling this website'll be live and then some day hopefully I'll be sending you enough traffic to make this worth it." That's kind of what's happened. There's been quite a few bumps in the road, but I basically launched it, it was just a side project. It wasn't a big company, I didn't expect it to turn into a start up.

Courtland Allen 0h 11m 37s

Who were these companies that you were convincing to sign up for that SEO link? How were you finding those people?

Tracy Osborn 0h 11m 45s

That's a good question. How did I find them? I want to say I did the scumbag thing where I looked at a competitor and just started emailing people competitor. I don't actually remember that process, I don't remember where I got it, but that sounds like what I would do.

Courtland Allen 0h 11m 57s

Yeah. You scrapped and you figured it out somehow.

Tracy Osborn 0h 12m 1s

I was like, I could do a better job than these other people.

Courtland Allen 0h 12m 4s

I don't think it's really that scumbaggy. I think it depends entirely on the nature of the email that you sent.

Tracy Osborn 0h 12m 9s

Right. I wasn't using the service. I wasn't using the inner wedding wire service to send the messages. I did some research, went to their website, found their actual email address. Wedding Invite Love was the first directory I launched and I actually ended up cloning it to a bunch of other ones, so then that's where all the different properties came about. There's Wedding Planner Love, we have Wedding Photo Love and you can get that they're all into individual areas, different type of vendor types for weddings. All those directories were launched from me just sending out 100 emails to people, being like, "Hey I'm launching something new, want to sign up for it?" I do it manually. It was definitely the do things that don't scale process to building these websites.

Courtland Allen 0h 12m 51s

What was your goal in these early phases? Were you thinking I just want to have a start up, did you have certain revenue targets you wanted to hit or certain lifestyle that you wanted to live?

Tracy Osborn 0h 13m 1s

When I first launched the side project, I don't think I had any expectations whatsoever. I was kind of like, oh this is cool, I'm going to learn how to program and maybe something will happen. I think, if I remember correctly, that at the time I was really into bootstrap businesses. This is, I think, when GitHub was completely… now they're funded, but they were the big one that was bootstrapped and I met a few other bootstrap people. I was like that's the way I'm going to go, and was just thinking okay I'll build this website and maybe someday it'll make money for me.

That summer, which was 2011, I think in January, I went to New York, this was like two weeks after the website launched, Wedding Invite Love. Again, side project. I had this lunch meeting offhand with Swiss Miss, Tina Roth Eisenberg who runs the Swiss Miss design blog. She was like, "What are you working on?" I'm like, "Let me show you this website I launched." Then she put it on her blog. All of her readers are designers and people that would be interested in something like Wedding Invite Love. That just launched Wedding Invite Love. That's the moment where I was like, oh this actually could be something legit, like people could actually use this.

I had so many emails and so many people signing up and I think my traffic just went through the roof overnight. That's when I decided to start spending more time focusing on it because I had that boost from her.

Courtland Allen 0h 14m 19s

You mentioned earlier that you were in school and you pivoted away from computer science to an art degree. You 180'd really.

Tracy Osborn 0h 14m 29s


Courtland Allen 0h 14m 30s

How much did your art degree contribute to your ability to get on the radar of people who liked design with your new website?

Tracy Osborn 0h 14m 38s

Definitely helped. That's actually the whole reason why I did something for wedding invitations. I'm not a weddings person at all. I got married three or so years ago and I eloped in Vegas because I was like, I've been working on Wedding Lovely for four years at this point and I was just like oh hell no, I'm not going to have a wedding. I see what goes into those things. I was like, no, that does not look very fun. Went to Vegas. Even at the time I was not like a big weddings person, but I love design.

I've always been into art as a kid and I've been building websites… You can't see me, but I'm doing air quotes, like websites. They're websites, but this is the 90's of when it was frame websites and GeoCities and Angelfire. I've been building websites since I was like 12, 1996 or so. I like designing websites.

When I quit computer science, the one shining part, the best part of computer science was when we were working on . I knew that I really liked working on the front end and what it looks like when someone clicks something and then something happens. When I went through art I was just like, okay, I'm just going to do just design and then I started working at a start up in university that did web design. I was like, oh I guess I'll do design and a little bit of programming.

The funny thing is is when I was at the start up, I was a front end developer and designer, so I was supposed to do HTML and CSS, and normally front end developers also do JavaScript, but I was traumatized from my time of doing Java. They're not the same thing whatsoever, but I still told them I refuse to do JavaScript. It was too close to programming. I had too much PTSD from this time in university.

Courtland Allen 0h 16m 10s

Yeah. You need time to recover, maybe a little bit of therapy.

Tracy Osborn 0h 16m 14s

Yeah. You say time to recover, this is still to this day, I have trouble with JavaScript. It was like this mental block in my head against JavaScript, which is a problem with all the JavaScript frameworks that are happening right now. I kind of feel like a dinosaur because I still promote Django. Yeah now I have a book on Django, but a lot of people have gone away from using something like Django or say Ruby on Rails in favor of these new JavaScript frameworks. I just have not been able to pick them up and I feel like such a dinosaur now. It's just like this weird mental block when it comes to JavaScript stuff. It's so frustrating.

Courtland Allen 0h 16m 47s

I think we're going to get into a lot more of your thoughts on that too because you've written books about Django like you said, books about design, which I can't wait to get into because probably one of the most common questions that I get asked, and that I see other programmers asking each other is, hey I got the coding skills, how do I pick up the design skills? Everything that I make looks like crap and I'm tired of it. I can't wait to get into that.

First tell us a little bit about what happened with Wedding Lovely and all these websites that you were creating. How did that all turn out?

Tracy Osborn 0h 17m 15s

Yeah. That summer of 2011 was like the rocket ship summer. Swiss Miss blogged about me, I started cloning the websites. By the way, this is still when I really couldn't code, so I mean cloning, I mean like literally taking the repository and cloning it. I had a whole new database and I had the same code on both of these repositories. At the time I had no… I couldn't think of a way to combine multiple websites under one project so I was like, screw this I'm just going to clone it and launch them. Then whenever I have to do a feature update, I will go and copy/paste it between all five, eventually eight, repositories. That's been fixed now. I got some help and I've learned a lot more since then.

It was a crazy summer where I was just launching all these directories. I got into the Designer Fund in San Francisco, which has kind of evolved since when I was a part of it. I was like their second "batch" when they're trying to help designer founders. I got into Designer Fund and through Designer Fund I was able to get an interview with 500 Startups. At the time, 500 Startups had no formal interview process, like YC's application process. I believe 500 has that now, but at the time, the only way you could get to 500 is to be introduced.

I had that contact through Designer Fund and I had my interview with Dave McClure and then another partner of 500 Startups at the time. The other partner had seen this post I had written the original post talking about finding a co-founder and I wrote a couple other ones afterwords, being like, co-founder didn't work out so I just built this website, and that also went big on Hacker News. Whenever I went to meetups in the Bay Area, they're like, "You're that weddings person that keeps showing up in Hacker News." I'm like oh my God I cannot believe this is my thing. Again, not being a weddings person myself, I just want to help small businesses do design.

Essentially, I got into 500 Startups as a solo founder. That was the moment when I'm like, oh I guess I'm not bootstrapping this anymore, I guess I'm doing a funded company. When I got that offer that was the biggest decision I had to make, was like do I want to change how I thought about this company and throw myself into this whole funded company stuff and fundraising.

Courtland Allen 0h 19m 25s

Yeah. That's when it gets real.

Tracy Osborn 0h 19m 27s

Yeah, seriously. It's scary. It totally changes the way a company is built too. I definitely don't regret my time in 500. It was hard because there was another weddings company in the same batch of us and they originally thought, "oh that's cool, these two weddings companies, they'll collaborate." We did not collaborate. We did not get along at all. This company has since moved on to other things, so that's my one claim to fame. Haha, I am still around. They on demo day three months later at demo day, they just kind of swept any investor that was interested in doing a wedding start up… there was a lot of drama during that time.

I was still rocket shipping. This is still the shining moments of Wedding Lovely. I had brought on a friend of mine to be a co-founder, we had an employee, we had an intern and then Etsy approached about an acquisition and that was amazing.

Courtland Allen 0h 20m 25s

Where was your company at at this point in time in terms of traffic and revenue?

Tracy Osborn 0h 20m 30s

So little. It was definitely going to be . I don't know. The whole acquisition thing was kind of crazy. Wedding Lovely was making revenue. It's that kind of thing where you're making revenue, but the sky looks like it's just endless, you can just go anywhere at that moment. The sky's the limit.

Etsy, I think they heard about me, they liked what I was doing, then they really liked my co-founder at the time. We went through this whole process of acquisition stuff so I just put the fundraising on hold. I was like, okay, you know what? This other company's taking all of the interest from 500 Startups for a weddings business and I have this opportunity to be acquired by Etsy, which I love Etsy, so I just threw myself in the acquisition process. That whole story, we need more than an hour. This whole thing has been crazy. That whole story, long story short, they ended up giving me an offer that was way lower than any of my advisors thought that they would give me.

I tried to be smart about it. I had advisors from 500 Startups and other friends, people who went through YC who gone through acquisitions and they were helping me out in this process. We all tried to guess, okay here's the floor of what they could offer based on what we were doing and then here's the super awesome, I'm super lucky offer. It turned out to be way, way less than anyone ever expected.

Courtland Allen 0h 21m 48s


Tracy Osborn 0h 21m 48s

There's nothing I could have done with that, I had to turn it down. It wouldn't make sense.

Courtland Allen 0h 21m 53s

How much time did you spend going through the process of talking with them and interacting with them before they finally gave you that low ball number?

Tracy Osborn 0h 22m 1s

I think it was like three months. It started out slow, right? Our original meeting in New York, which then turned into a meeting in San Francisco with some other people. Then we had demo day end and then they flew me and my co-founder in for the day of meetings at Etsy where we met all the big wigs and Chad who was the CEO. We had this super long meeting with him that finish everything so he had to come back to us and continue our meeting and then a big dinner at the end of the day. We just went to our fancy hotel. We're staying at the fanciest… The places celebrities stay in Manhattan. It was amazing. They booked us this crazy hotel.

It was just like on the top of the world, wow, we totally got this. We are going to be acquired by Etsy and I'm going to have that stamp next to my name, like acquired by Etsy on my future start up resume. Turning that offer down was just devastating. We thought we did everything right. I thought everything was aligned. We tried to negotiate it up, like, "Don't you mean a little higher? and they're like, "Nah. We're going to move on." They didn't negotiate at all.

Courtland Allen 0h 22m 1s


Tracy Osborn 0h 23m 13s

It was crazy and so depressing.

Courtland Allen 0h 23m 17s

Yeah. I can't imagine how upsetting and depressing that would be. How do you recover from that? That's three months gone basically. You put off your fundraising for that, you had your hopes up.

Tracy Osborn 0h 23m 29s

That's when it started going downhill. That's when most people probably would've shut down the company at this point. We lost interest in fundraising. At this point we'd been distracted, the company didn't grow as fast as we said it was going to, try to look at fundraising, but we lost the momentum.

We're like, okay, cool, launched this other product. At the time it was just Wedding Lovely businesses. I decided to build in this Wedding Lovely planning app so then we could work with users, diversify our customers, and then the users that we bring into this planning app would start working at the businesses we work with. It sounded like a win, win, win thing.

We said, okay we'll launch this planning app and when that rocket ships then we'll do the fundraising process again. Launched the planning app, didn't rocket ship, started running out of money, had to lay off the employee, intern went at her normal time so that was fine. Then my co-founder just quit, out of the blue to me. Sat me down, said she has another job, and then she's gone at the end of the week.

Then it was just me. This is like six months afterwards, something like that, six to eight months. Lost everything and just so… I don't know. It's just like that last year was so many highs and so many amazing things that are happening and then it just all went away. It was a really, really hard time for me. I was lucky that the way that Wedding Lovely is built, it wasn't like we had a lot of support requests. We didn't have to do things day to day, it was kind of like we built it and it started running itself.

I think if I had to deal with support requests or I had to continue working on it, I probably would've shut it down, but I ended up kind of just checking out for a month and let it do its thing. I just was depressed. I think this is December, did nothing that month. Wedding Lovely just kept trekking along. I didn't shut it down because I didn't really have to, but I had to step away because it was just really depressing time t have all these expectations just crumble away.

Courtland Allen 0h 25m 36s

Yeah. This is point number two in your business, where I think most people would be like that's it, I'm done, I'm out of here.

Tracy Osborn 0h 25m 42s

Yeah. Most reasonable people.

Courtland Allen 0h 25m 44s


Tracy Osborn 0h 25m 46s

You fail fast, just shoot it, move on, move on with your life. Shutting it down, it was also, it felt like the final admittance of failure. I was like, maybe [inaudible] this.

Courtland Allen 0h 25m 58s

I think you hear a lot of stories about perseverance. You hear the famous one is the Airbnb story about how these guys spent years trying to get their business to work and it just kept not working and they were going into debt and nothing they're doing is working, they're selling cereal just to finance their business. Then it's a happy story at the end, it all works out. Every time I hear that story I'm like I for sure would've quit. That's crazy they should've quit.

How did you decide after you came back from your month of doing nothing that you weren't going to quit?

Tracy Osborn 0h 26m 31s

I'm going to briefly summarize. That briefly quit was like two years in and I'm seven years now so there's a lot of middle ground. It's funny because I've done podcasts over the year where I've told this story and again, spoiler alert, this year I actually am like, wow this year has been a success and every other year when I was on a podcast I'm like, "Yeah we're doing pretty well." It was like me, I don't know, pumping it up a little bit.

It's funny looking back on those five years where it was just like the company just kind of plotted along, didn't really do much, but it wasn't going downhill. I was lazy, also hopeful, also hoping that… Actually I should back up. One of the reasons why I kept this hope is that it's a marketplace and it works better the more businesses you have on the marketplace. It's more useful to people the more businesses that get on there. I didn't have funding in order to kick start it up to 100,000 businesses, but people were still signing up for it and people were still sending me messages saying they found use out of it. I was like, well, I might as well just keep it going. It was still making some amount of money and that some amount of money was still coming back to me.

Over the last five years it was like, okay, I'll work in this myself and people seem to be finding some sort of joy on it and I do enjoy the process of running it and doing marketing, but that's one of the reasons why I wrote the books was that after years of just having this thing plot along, it was like, oh crap I need to find something new to work on. I wanted to write. I had this ideas about how programming should be taught based on that experience in computer science, based on experience of teaching myself, and then also my experience of working at Django the last few years.

I was like, okay, I'm actually going to create this whole other project. I'm going to write this book called Hello Webb App, teach Django and web app programming the way I think it should be taught because A, I think it should be done, but B, I also kind of need money now. The Wedding Lovely is still not… I think until this year, like I said, it's the best it's ever made. It's probably going to be on track to make 60 to 80,000, something like that. It's mind blowing because all those years before it was maybe making 15 to 20,000 per year.

Courtland Allen 0h 28m 44s

Wow. You were just surviving off of that.

Tracy Osborn 0h 28m 47s

Yes. Pretty much. I was lucky to be in San Jose. This is going to sound amazing and I'll say this, there is a story behind this that makes it not as amazing as it sounds. I had a five bedroom house in San Jose for free, it was a family's home. I just worked, my husband worked on his start up there, I worked on my start up. I didn't have to worry about rent, thank goodness, so lucky that I had that because I think Wedding Lovely would've had to shut down if I had to pay rent. I was able to cut my expenses really, really low. I brought in a roommate, that person was paying me rent so I had a little bit of income from that, and kind of just made things work over those years.

Courtland Allen 0h 29m 22s

That's huge. I very rarely hear stories about people bootstrapping in Silicon Valley or in San Francisco just because of how expensive the rent is. That alone will kill your bootstrapping ambitions.

Tracy Osborn 0h 29m 32s

Yeah. Totally. Again, it's not just like I have a rich family , like hey use this house. There's a story. There's not a lot of good parts of it, not going to say it here. I'm just going to say to anyone who's like, "Wow she's so lucky." Yes I'm lucky, but there's also a story.

To jump to the end of the story, this last year, it's been kind of crazy because just plotting along and I'm like, whatever, and sometimes I get tired of it. I was actually legit thinking about last fall, maybe I should finally shut it down because it's continuing to plot along and it's taking up these cycles in my brain and it's still running and people seem to enjoy it, but there's so many other start ups that have launched during that time that I launched it and then since then that seem to be doing so much better than me. I don't have that drive anymore to make Wedding Lovely a complete success anymore. I'm just so weirdly burnt out, like still working on it, but not.

At that time, someone who worked with me part-time online came back, I couldn't afford to pay her full time, came back to me after a good year of not working together. She messaged me asking me if she can come back as part-time because she loved working on Wedding Lovely so much that she was going to make it work elsewhere. She was going to pick up other writing jobs, online writing jobs or editing jobs or something on the side so she could work on Wedding Lovely part-time. I was like, you know what? This person is passionate. I lost this passion over the last seven years of working on this because it's just been plotting along and I've… doing it myself, I just couldn't do it anymore. Here's this person who wants to come back.

I took what I was paying myself, which I think at the time was 20,000 a year and I'm like, okay, 20,000 a year, part-time work, I gave her access to all the financials. I was like, "You can see the exact state of the company, you can see everything, you're basically in charge. I'm not paying myself anymore." That was the moment when Wedding Lovely started taking off finally. It's like I needed to fire myself. It's ridiculous. Looking back on it, I've been plotting along in this company for so long and it took me finding someone who's passionate about it again. I guess I was holding it back by losing that passion.

Courtland Allen 0h 31m 44s

That's a crazy story. Did you just completely stop working on it at that point?

Tracy Osborn 0h 31m 49s

Pretty much. I guess I was fixing bugs. The book stuff started taking off, which we haven't talked about, but the book stuff started taking off. My speaking career started taking off. Again, it was just that laziness and not shutting the website down. She started working on it part-time. There was a person that was working for me part-time as basically a WordPress assistant and she was going to quit because she's been doing WordPress stuff for me for six years. I was like, "Okay, you work with Jannie." this person is , I'm like, "You work with Jannie." Jannie worked with her to change her duties, what she was working on. They started working together. I had hired a personal assistant in the Philippines, like you do as a bootstrap start up, and she was full time. They started working together. It's the three of them and, again, the company just is making more money than it's ever had before, it's getting more traffic than it's ever had before. The three of them are, as far as I can tell, super happy.

I think last week I moved Jannie from part-time to full-time because the company could suddenly afford it. A couple days ago I looked at the financials for the rest of the year and I'm like I actually can start paying myself again. I'm paying myself very little as a contractor. Those three are definitely the people who are in charge of the company and I'm just advising it. It's mind blowing that a year ago…

Courtland Allen 0h 33m 6s

That's ridiculous. Congratulations. That's so good to hear though.

Tracy Osborn 0h 33m 11s

Yeah. I don't know. It makes me so happy actually. I'm so much happier running the company and having people who are passionate about it and every now and then we'll have this stellar month and so I'll just send them all bonuses. It kind of feels like that stack of 20s in my hands and I'm just flinging the money about. I'm making these three people really happy, as far as I can tell. I think I might change my passion in the company or maybe my passion has been reignited to make these three folks, and hopefully any future employee, make them happy and give them something they can work on.

They have that passion and now it feels like instead of me being passionate about Wedding Lovely, it's me being passionate about helping them build this company together. It's changed in my mind. I don't know. It's really cool after six years, whatever, seven years of plotting along in this company, having everything change what feels like overnight. Finally, these awesome things are happening since the last awesome thing, which was the Etsy stuff.

Courtland Allen 0h 34m 14s

Yeah. I think some people will probably think this is controversial and some people think it's obvious, but there's nothing like making somebody that you know, or somebody happy on a very personal level where you can actually hear their story and see how you're affecting them. It's so different to do that. Doing that I think is so much more impactful and feels so much better than even making a website that reaches some gigantic number of people where it's just a number, it's intangible.

If you're Mark Zuckerberg and you create Facebook, I'm sure it feels good on some level to be like, I've reached X billion people, but that's just a number. It doesn't feel as great as actually hearing people talk about how you've helped them or having somebody that you're working with super passionate about this job that you basically created.

Tracy Osborn 0h 34m 57s

Yeah. I can see them talk on Slack or on the emails and there'll be a problem and they work together to fix it and I'm just like, holy crap. Sometimes I call my minions, and I don't mean to be derogatory, but here are these people that are doing the job that I was doing before and they're doing it better than me and they're solving problems better than me, especially since I was burnt out. They can ping me if they have questions or they want to use some of my background experience on Wedding Lovely, but they're definitely going their own direction and doing way better. It's such a good feeling.

Courtland Allen 0h 35m 30s

One of the things that you mentioned was that by the time you got to this point where you were a little bit burnt out on Wedding Lovely, you were having your flame ignited in other areas. Public speaking was taking off for you, you were writing your book and that was doing really well. How did you get into writing your book and what kicked off that process?

Tracy Osborn 0h 35m 48s

Yeah. The books came about because I was burnt out, I needed something else to work on and I didn't want a job. Throughout this whole process I've determined that having a day to day job is just not for me. I got used to making my own hours and working weekends when I want and working nights when I want and taking off the afternoons when I want, that kind of stuff.

Courtland Allen 0h 36m 9s

It's really nice.

Tracy Osborn 0h 36m 10s

Yeah. Exactly. I was like, okay, what can I do to supplement my income so I don't go completely broke and have to get a job? At the time, maybe not so much today, I think people are so much into courses now. When I decided to write Hello Web App, which was like two and a half years ago, books were the big thing. I think they're courses now, but at the time, this is when Nathan Berry was releasing a bunch of books and getting big on Hacker News. I think Nathan Berry is actually my inspiration for Hello Web App because he wrote a lot about the process of writing a book and then how many buckets of money he was making from his books at the time. I was like, damn.

Courtland Allen 0h 36m 10s

Yeah. He just told everything.

Tracy Osborn 0h 36m 50s

Yeah. I loved it. I'm like, oh I could totally do that. Okay. My background in design definitely helped because in university, my graphic design courses, I took an editorial design course. The process of formatting a book was super fun, I loved it. It's something I don't think a lot of people would be into, but I just love the little nit picky parts of designing and changing the type and making sure paragraphs are perfect. It's weird.

Those two things came together. I was like, okay, i need to make money. Here's Nathan Berry making buckets of money and I think I have an idea for teaching people how to program that is different than what other people are teaching. People were saying here's how to program with a specific project idea and I wanted to build something that people could use as a template in order to build what they were passionate in.

Last but not least was in Django, the framework for Python, which still to this day I am the biggest fan of Django. I think they're doing still really great things for helping people build web apps and abstracting out all the little nitty gritty things that are background. I'm a huge fan of Django for teaching people how to code, especially when it comes to web apps.

Yeah. That's where it started, it just snowballed into this bigger thing. I thought about pitching a publisher on this, and I actually got a publisher offer for the idea of Hello Web App. I think I wrote the first 2,000 words, I submitted it to A Book Apart and they're like no. This is the people who do all those fancy books, A List Apart and An Event Apart. That was my real dream. I was like, okay I want to become A Book Apart author because that means I've made it. They're like no. I was like, okay what do I do next?

I submitted it to another publisher and they gave me their standard terms, which was something like $8,000 advance for 5% royalties. When I looked at that and then Kickstarter was a thing and I looked at Kickstarter. Kickstarter's essentially, if I can do a successful Kickstarter, the money raised from a Kickstarter is essentially an advance, but then I also keep 100% of the royalties. I lose someone to design and publish their design and format the book for me-

Courtland Allen 0h 39m 3s

But you like that part anyway.

Tracy Osborn 0h 39m 4s

Exactly. Then I was like, shit. I just told the publisher thank you but no thanks and threw myself into the Kickstarter process, which also is a good way of proving an idea. I scheduled the Kickstarter around, I believe, PyCon, which is the biggest Python conference, and launched the Kickstarter. Went to PyCon and I just found all the big wigs in Python. It was like, "Hi. I'm Tracy. You don't know me. I'm doing this Kickstarter. I want to write a book on Django, which is Python, can you help me tweet out the Kickstarter link?" which was cool. It was a really cool way of hustling that whole process. Kickstarters, done three now, Kickstarters are so much work to get them out right.

Courtland Allen 0h 39m 48s

They look exhausting just watching the videos that people make for their Kickstarters and all the awards that they give out.

Tracy Osborn 0h 39m 53s

Oh yeah. I had a friend of mine who did a Kickstarter himself while I was doing a Kickstarter for my third book. We got in this gigantic fight. It's just because both of us are just so stressed out during Kickstarters. Afterwards, it's like okay the whole reason we had this fight was not because we're not friends, it was because we're just stressed out from running these Kickstarters. Maybe we shouldn't talk to each other until both of our Kickstarter campaigns are done because this is not working out.

Courtland Allen 0h 40m 17s

Yeah. I think it's really interesting that you decided to write a book about Django. If you look at the beginning of your story, way back when in 2011, here you are copying and pasting all of your code because you're not sure how to duplicate it and reuse it. A short time later you're writing a book teaching other people how to use Django. Where did you get that confidence from and how much had you improved as a programmer in that amount of time?

Tracy Osborn 0h 40m 42s

I've improved as a programmer, but I also strongly feel that beginners teach other beginners better. When you're an expert programmer, you lose some of the… You forget how hard it is to learn programming when it doesn't come naturally to you. I definitely wrote Hello Web App as a beginner. Hello Web App itself is very simple and again, it's just the process I did to launch the first version of my website.

All it is it walks someone through building a website, adding a database, getting website pages up. The other cool thing it does is that I really focus on websites as a result rather than, say, command-line. I don't like programming tutorials for new programmers that just says show us everything through the command-line because I don't think that feels real to someone who's not used to the command-line. It's like build a website and then launch on . That's essentially what Hello Web App is, and then you have some Django things in there.

Courtland Allen 0h 41m 37s

Got it.

Tracy Osborn 0h 41m 38s

Yeah. As a beginner it was easy for me to teach because it was all beginner stuff. It was scary because I did some tutorials for Hello Web App at PyCon and DjangoCon the year afterwards and I always had to make sure my friends who were good at Python came with me because people would ask me questions I had no clue how to answer because I was still a beginner.

I'm still not an expert Python or Django programmer. Now that I'm doing public speaking, I actually did a keynote at EuroPython this year and it was essentially on this whole problem of I'm not an expert programmer, I'm not an engineer, I can never be hired by someone, by Google or Facebook, but I've written books that teach people how to program. I feel like I have really contributed to the Python and Django communities, but I am not an engineer. That's what my keynote explores is this problem where people think that you're either an engineer or not or you're a smart person or not.

Courtland Allen 0h 42m 35s

Yeah. It's not so black and white and you can contribute a lot without having to be a super deep expert in any one area.

Tracy Osborn 0h 42m 43s

Yeah. Just to call out EuroPython on this actually, their badges were perfect for this because they're the largest Python conference in Europe and their badges had the saying where it said Python Power and you could do one to five stars. I was like, this is what I mean. Here I am doing a keynote at a major Python conference in Europe and I put three stars out of five because I didn't want to be like two stars, what are you doing on stage if you only have two stars. That was the thing I don't like is when people say beginner, intermediate, advanced programming when there's so many different things you can do with programming like write books or run tutorials or teach beginners or start a start up.

I built all of Wedding Lovely not feeling like an expert programmer, but I was doing company work. The code was probably atrocious, probably still is atrocious. It's a lot better. It worked, right?

Courtland Allen 0h 43m 32s

Right. The main point to starting a company is not to write the world's most beautiful code and be the best software engineer possible, it's to produce something of value that customers want and will pay you for.

Tracy Osborn 0h 43m 42s


Courtland Allen 0h 43m 43s

I think a lot of people get confused about this. I talk about it ad nauseam so I won't go into my whole diatribe here, but…

Tracy Osborn 0h 43m 51s


Courtland Allen 0h 43m 51s

You did it right.

Tracy Osborn 0h 43m 52s

It's good to hear that in hindsight. At the time it did not feel like it was the right thing. When I teach people, I haven't done a tutorial in a while, but sometimes I'll do a tutorial based on the books I wrote at these conferences and I always pull up the live Wedding Lovely code. Even as beginners people who don't… they're very new to this, they can see how crazy the code is. It doesn't look like those pretty examples they would see on Hacker News. They can see that here's a website that is running and is making money and here's what the code looks like. As beginners, you don't have to worry about your code being beautiful and perfect, you just have to worry about whether your code is working.

Courtland Allen 0h 44m 32s


Tracy Osborn 0h 44m 33s

And then just go from there.

Courtland Allen 0h 44m 34s

I think another thing that people struggle at in the beginning is design. You wrote Hello Web App, you wrote a follow up to Hello Web App, and now you've written a new book, your third, called Hello Web Design. The idea behind it-

Tracy Osborn 0h 44m 49s

Yeah because I'm clever. Yeah.

Courtland Allen 0h 44m 49s

You got a theme and you're sticking to it. The idea behind it is that you want to help people who don't have a design background to learn the basics and the shortcuts behind good design. Is that an accurate description?

Tracy Osborn 0h 44m 59s

Yeah. I mentioned briefly I've been doing a lot of public speaking recently. You release a book and then you can use that to start speaking at conferences and then you speak at conferences and then you can use that to release more books. It's something that people do, I fell into that myself. I did a bunch of Hello Web App presentations and then I made this new presentation I called Design for Non-designers. With Hello Web App, again, I thought I had something new to say that could help people learn how to program. Then I started thinking to myself, what if I could teach design in a way that I wasn't seeing it being taught by other people.

In both of these fields, even though they're the opposite, I do not like best practices. I don't like it when experts try to teach someone the best way to do things. Hello Web App I am teaching people not the best way to do programming, but they can learn that at step five. I thought if I take this idea behind Hello Web App and apply that to design, how can I teach beginners how to design that defies best practices and teaches them short cuts. I think if you get someone to that initial success, it's more likely they'll continue with whatever they're learning.

That's where it started ruminating in my head. Okay, maybe there's another book in me, maybe there's something new that I could teach. I originally did it as a conference presentation. This was last year. I probably gave it like 10 conferences. It was crazy. All of them were picking it up, which was amazing because I got to travel a lot during this time. I wasn't being paid, but I went to Berlin, I gave at , I gave it in Hollywood at a GitHub conference. It was a great way for me to test that people were interested in this idea of… They were interested in what I had to say, this design for non-designers, these shortcuts that I've figured out would be the best way to help someone jump into design really quickly if they know nothing about design, just having some knowledge about the web.

That's where it started was last year. Every one of those conferences, I'm like I'm going to write a book about this. I only started working on the book this year because it got really intimidating. I kept telling more and more people about doing it, which this works for everything, when you tell a bunch of people you're going to do something, it makes it harder to do it. Start ups, writing a book, anything. I told way too many people I was going to work on this book and then I was like, oh no, I actually have to do it. In January I did a Kickstarter and I raised 22,000, which is pretty damn awesome.

Courtland Allen 0h 47m 29s

That's huge.

Tracy Osborn 0h 47m 30s

Again, it's a really good advance. I started working on it before the Kickstarter, but I'm still working on it today. It's delayed. Sorry Kickstarter backers, I'm working on it as fast as I can.

Courtland Allen 0h 47m 41s

It's not a Kickstarter if it's not delayed.

Tracy Osborn 0h 47m 42s

Right? Actually with the first two books, I did Kickstarters for them both, every time I expect this. Every time I get someone who emails me going, "So I paid for your book, but I haven't got it yet. Can you tell me what happened to my book?" I'm like, "Uh, it's a Kickstarter. You're not paying for a book. I do updates." Uh, people.

It got so stressful. Hello Web App was actually a year delayed. That was my fault. These emails would happen and whenever they popped in, as soon as I saw "You have a new message from Kickstarter" I grab my husband, I make him read it, and to let me know what it said because I just couldn't read those anymore because it was so depressing to have these people being like, "Where's my book? Are you ever going to release this?" People are happy now.

Courtland Allen 0h 48m 27s

It sounds like you've gotten really good at Kickstarter too. Raising $22,000 for a book on web design is no joke.

Tracy Osborn 0h 48m 33s

Yeah. I was trying for 30. That's always the thing, right?

Courtland Allen 0h 48m 37s

Yeah, but 22's huge.

Tracy Osborn 0h 48m 38s

Yeah. My minimum was 15, I hit 22, I was trying for 30, but that's always the raise, try to go higher. It's like put your minimum at half of what you want, but hope that you're going to hit between your minimum and what you actually want. I could do a whole podcast on Kickstarters. I've learned so much from Kickstarters over the years.

Courtland Allen 0h 48m 58s

You mentioned that you were in the cycle of speaking and writing books and then using the popularity of your books to get more speaking gigs, et cetera. How much did that help you-

Tracy Osborn 0h 49m 7s

That also slows me down.

Courtland Allen 0h 49m 8s

It slows you down for sure, but you're also building an audience I presume and meeting influences who can help you promote your books and your Kickstarter. Give us a quick overview of some of the things you did to drive traffic to your Kickstarter page and convince people to contribute.

Tracy Osborn 0h 49m 25s

I will say that I look back on this last year promoting Hello Web Design, I think I could've done a better job. I think everyone will say that for their stuff. For me, there was an opportunity to really sign people up for email lists, and that would be a really good thing if I really worked on it and I actually didn't do as much. My Hello Web Design email list I think has like 20 people on it. It's kind of silly considering the Kickstarter. I still have the Kickstarter list, it's a separate list, I don't immediately subscribe them to this main marketing list. Then I have the Hello Web App email list, which I think has like 3,000 people.

Just FYI, all these conferences I should've done a better job of being like, "And now sign up for the email list." I really should've done that a little bit better. That said, during the Kickstarter, I decided to try something new and it wasn't 100% successful, but I'm glad I tried it. I didn't schedule it during a conference I was giving, I decided to try to do this little tour aspect where I would go to companies in New York and in San Francisco, give an internal talk or an evening talk, and be able to talk about the Kickstarter during those talks.

Ideally those companies would be paying for me to fly in because I was going to give a talk at their company and then I would have this opportunity to promote the Kickstarter and then hopefully also get the company to help back the Kickstarter. It sounds like a really good idea considering my public speaking experience and it was also I wanted to have corporate speaking experience on my future speaker's resume. I thought this would be a really good opportunity for me to combine the Kickstarter with this idea I wanted to do more corporate speaking. It didn't work out.

Courtland Allen 0h 51m 5s

What went wrong?

Tracy Osborn 0h 51m 5s

I really wish it did. I did one internal event in Toronto, that's where I live. I'm originally from California, but I moved to Toronto last summer. I did an internal event at this company, actually that company, PagerDuty, that was awesome, they actually backed the Kickstarter so that was successful. I didn't have to travel for it so that was awesome. Then I did an event in New York City. I'm not going to say the company's name because that's just mean, right? I don't want to be like, I had a bad experience and say their name.

Courtland Allen 0h 51m 5s

Yeah. No need.

Tracy Osborn 0h 51m 35s

Yeah. There was a big company that did an event internally and they're like, oh we're not going to pay, but you can do this talk. The talk was like 10 people, I had no idea it was going to be that few people.

Courtland Allen 0h 51m 46s

Oh that's rough.

Tracy Osborn 0h 51m 47s

Yeah. It ended at noon and they just kicked me out. I'm like, not even lunch?

Courtland Allen 0h 51m 51s


Tracy Osborn 0h 51m 51s

Come on, big company, I know you have a kitchen and all the people are going and getting their lunches and whatnot. I knew it was ending at noon and I thought the chances were high that at least I get a meal out of it and they just basically just shoved me out the door after this talk. I was like, oh I regret spending the money to fly to New York and stay in New York and get up here for this stupid event at this company. I was really mad. I feel betrayed. I emailed them saying, "Okay will you at least back the Kickstarter?" and they're like nah. I'm like, oh my God I did so much work for this.

That didn't work out, but I was able to salvage it by booking a local Python event, Python meetup. I was able to go to the Python meet up and give a talk and then promote the Kickstarter there. I flew to San Francisco and gave a talk at Stripe. That was awesome. Stripe didn't back the Kickstarter but they did an open event, a public event, and I think this is the first time, and only time, that I've headlined a event just around me. That was pretty awesome for my speaking resume.

I gave my design for non-designers talk. Oddly that's probably the worst talk I've ever… I've given the talk multiple times and I just remember bombing it. For some reason I got really nervous. Maybe not bombed it, but it wasn't as smooth as my other talks. It was still cool. I was able to go to San Francisco, I talked to probably maybe 100 people at an evening event at Stripe and I was really happy that they were able to support me in that way and host this event and bring in food and all that. That was cool.

Courtland Allen 0h 53m 19s

Yeah. That's super cool. I work at Stripe and I had no idea that happened.

Tracy Osborn 0h 53m 23s

Yeah. It was, oh my God, I'm going to forget his name, Romaine. He wasn't the person… He was surprised by it too. He's the at Stripe. I think I surprised him because I just emailed someone, some contact I had there, like, "Hey want to do this?" and Stripe's like, "Sure." Yay Stripe. I'm a huge fan.

My second book for Hello Web App, I never really mentioned this. Hello Web App is a tutorial, Hello Web App: Intermediate Concepts just does individual chapters of advanced things or intermediate things call it. One of them is on Stripe. I did that because Stripe is amazing and I wanted to help people use Stripe.

I'm not paid by Stripe, they didn't pay for the chapter either, they backed the Kickstarter campaign and they did it as a silent partner. They didn't want it to look like they… they didn't sponsor that content. It was all me, but they backed my Kickstarter and helped me run this event and they've been big supporters of me, which has been awesome. Yeah. Public thank you to Stripe.

Courtland Allen 0h 54m 10s

I think the vibe I'm getting from your entire career, your entire last seven years, is that you're pretty scrappy person and you figured out how to make things work and stick with them regardless. The fact that your strategy for getting a Kickstarter fund didn't really work and yet you still got $22,000 as an advance to write a book is a perfect example.

Tracy Osborn 0h 54m 28s

So many emails.

Yeah. There's a whole other thing I can say about Kickstarters. That was just one tactic I had. I need to write a blog post about my new marketing tactics for Kickstarters. One of the things I don't see people talk about is that a Kickstarter's generally is 30 days. You have essentially four weeks and the beginning of a Kickstarter and end of the Kickstarter are very different, they're the hype. There's this middle doldrums period where if you're running a Kickstarter the first week you're like, yeah, and then the second week you're like, uh oh, and then the third week nothing happens. You're like, oh my God I'm going to fail. The fourth week comes along and then it starts taking off again because people get excited because it's about to end.

Courtland Allen 0h 55m 4s


Tracy Osborn 0h 55m 6s

It's the natural thing that Kickstarters do. I had set up my marketing tasks depending on the week. There were things I would do on the first week because it made sense, like emailing personal contacts, emailing email lists, but there had to be things that were scheduled specifically for those middle periods. I knew the doldrums were going to come. That's only because I did this before, I had this experience of running Kickstarter, that I was able to anticipate that middle , which always sucks. That's when I scheduled those trips so I could continue to do marketing and continue to promote the Kickstarter, even when it's arguably harder to do. I did ads, I had those email lists, there's a lot of things I did. I really should write a blog post.

Courtland Allen 0h 55m 51s

Yeah. It sounds like it could be a book. You could do a Kickstarter for a book about how to do a Kickstarter.

Tracy Osborn 0h 55m 58s

It's funny. I do this public speaking a lot, I had that design for non-designers talk that went big, I give a talk I call Marketing For Developers. Essentially I got into this whole I'm going to teach beginner concepts to a different group of people, generally developers. I have this Marketing For Developers, a lot of people have been like, oh so you're going to have Hello Web Marketing or whatever, that's going to be your fourth book.

Here's the thing. With marketing and these other talks I give, I don't have that something different, like the design I have these shortcuts, these things that people aren't teaching. With the Hello Web App I have something that people aren't teaching that I'm teaching. I haven't figured that out for anything else yet. I can parrot what other people are saying for Kickstarter, but everything I've learned people have said before. I haven't figured out what I could say that's different. That's what I'm waiting for. For any future book is maybe a Hello Web Design will be my last one. Or maybe there's other ones. I just have to figure out… That really what propels me to write a book is when I figure out what I can say that's different than other people are saying.

Courtland Allen 0h 57m 0s

That makes perfect sense. We got diverted on this topic of Kickstarter, but I personally would really like to know, what are some of the basics and the shortcuts behind good design?

Tracy Osborn 0h 57m 11s

Essentially I try to teach a lot of the online… There's a lot of online resources that can help someone out. When you look at design books, when they teach beginners, they're like oh typography, let's go into the history of typography and all the terms that are in typography and they start teaching you the background and then what everything means and it gets really overwhelming.

If we're doing type online, the presentation started out being like typography is a huge area, so let's look at free fonts online because this is base for people who are working on the web. Let's look at Typekit, or Typekit's paid, so Google Fonts essentially. Google Fonts is overwhelming, so there's these websites where people curate the best Google Fonts. Let's go to these places that have 20 fonts that you can choose from rather than, say, 100 as a person who doesn't know design. Going on there it's going to help you narrow down choices and make better choices by using what other people have curated.

I'm like, use that shortcut. Don't feel bad. If you're designing something for the first time, you don't want to learn the history of typography, you just want to have a good font. How can I help you find something that works for you, narrow down the choices, and make it easier for you as a beginner designer?

Courtland Allen 0h 58m 28s

That makes a lot of sense. You're just making the entire process less intimidating or less aggressive approach. You don't need to be the world's best and most knowledgeable designer just to get something out the door that looks good as a beginner.

Tracy Osborn 0h 58m 37s

Yeah. That's the thing with design. The best way to learn design is not reading about the background of design, best way to do design is by doing design. You have to do design over and over and over. If there's this huge mountain ahead of you where people are saying, let's learn design, they teach you everything that's the background, the mountain gets even higher. It's like how can I make this mountain a lot smaller so then you feel comfortable actually starting to do design. That's how you'll become a better designer because you'll feel comfortable about doing it, your first one is probably not going to be as good as your second one and second one's not going to be as good as your third one. You're just going to build and become a designer that way.

I was like, how can I teach someone to start, get on that process and shorten that mountain, make it easier for them to summit?

Courtland Allen 0h 59m 18s

Let's say I'm a programmer and I just launched my side project and it's totally horribly designed? I have no design skills whatsoever. What are some things that I can do, what are some more tricks and shortcuts I can take to make it look better in a short period of time?

Tracy Osborn 0h 59m 33s

I tried to narrow down when it comes to visual design. The two parts of the design process is making sure it works, because you can have a crappy design, but if it still works well, then boom it's a good design. A lot of people rely too much on aesthetics. That said, when someone says how do I become a better designer, they're thinking probably about aesthetics.

Courtland Allen 0h 59m 52s


Tracy Osborn 0h 59m 52s

I try to narrow it down to just one concept, which is to reduce clutter. All the principles in the book are based around the whole clutter, like the visual principles, are around clutter. It's like you add a grid so things line up and then having things lined up under this invisible grid reduces visual clutter. Then when it comes a type, instead of doing a bunch of different fonts, which a lot of newbie designers do, let's narrow down to just two fonts that you use in your design, and that also reduces clutter.

Then you go into colors. Take a color palette, narrow it down to a smaller color palette and just use the same colors over and over. I'm paraphrasing and making things a lot shorter, but essentially color, how do you reduce clutter with color. How do you reduce clutter with white space, how do you reduce clutter by reducing the length of your content and making things easy to read? It's not just aesthetics, but it's also what you're writing and that's going to help your website work better, which is really truly the thing you need to do is making sure what you're designing is working well, not just looking good. It all ties together.

Courtland Allen 1h 1m 0s

That's perfect. You heard it here. A lot of people post their landing pages on Indie Hacker's forum and a lot of people want design advice and all the things that you've said, I think people would greatly benefit from learning more about. Can you tell people where to find out more about you and where they can go to order Hello Web Design and your other books too?

Tracy Osborn 1h 1m 18s

Awesome. Yes, happy to help. One little anecdote I think actually would be funny is that Hello Web App was only named Hello Web App because I found out that the URL as available. Like, boom got the name for my books. I can get hellowebapp.com. Then when I launched Hello Web Design, I was like, ah crap.

Courtland Allen 1h 1m 36s

That's it.

Tracy Osborn 1h 1m 36s

What do I do here? Hello Web Design is not available, what do I do? If you want to go to the website dedicated for the book it's hellowebdesignbook.com. That said, I have now an overarching domain for everything, hellowebbooks.com. That will lead you to Hello Web App or Hello Web Design, which you can pre-order now. I'm in the process of building a video series, which actually is going to look at landing pages and talk about the principles in the book and how they can apply these landing pages to make them better. There will be a whole video package that I'm working on right now. That will be maybe interesting to Indie Hackers.

That said, actually I'm going to pitch something. I'm in the process of planning this video series, so if you are listening to the podcast and you want me to review your landing page or your design and would be interested in having it in this video series, send me an email and that probably would totally work out because I haven't put out a call for people to send me stuff to review yet.

Courtland Allen 1h 2m 34s

That would be awesome. Could I convince you to come onto the forum on Indie Hackers and we'll make a thread and people can also get in touch that way?

Tracy Osborn 1h 2m 41s

Yes. That would also be very proactive.

Courtland Allen 1h 2m 43s


Tracy Osborn 1h 2m 44s

I probably should do that. I'm focusing on getting the editorial design for the book done and the cover for the book done, so this video thing is something I'm working on but that's like two weeks from now.

Courtland Allen 1h 2m 56s


Tracy Osborn 1h 2m 56s

Yes, I will do that when I can focus on it. That's Hello Web App, hellowebbooks.com, Wedding Lovely has all the vowels, it's exactly as it sounds, weddinglovely.com. My personal website, my user name I use online is limedaring, not limedarling, common mistake. I now preface all of my presentations with, "I'm limedaring, not limedarling." It's interesting. I can't change my username now, people will be confused.

Courtland Allen 1h 3m 25s


Tracy Osborn 1h 3m 27s

Limedaring.com, Twitter limedaring, my DMs are open. I love it when people email me, love when people DM me. Look at my books, send me messages, ask me questions, I love it.

Courtland Allen 1h 3m 36s


Tracy Osborn 1h 3m 36s

Happy to help people.

Courtland Allen 1h 3m 37s

If you enjoyed listening to this conversation and you're looking for a way to help support the Indie Hackers podcast, then you should subscribe on iTunes and leave a quick rating and review. It only takes about 30 seconds, but it actually really helps get the word out and I would personally appreciate it very much.

In addition, if you are running an internet business or if it's something that you'd like to do in the future, you should join me and a whole bunch of other internet entrepreneurs on the IndieHackers.com forum. It's basically a community of like-minded individuals just giving each other feedback and helping out with ideas and landing pages and marketing and growth and other internet business related topics. That's www.indiehackers.com/forum. Hope to see you guys there.

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